


Day Eleven: Crossdressing

by TobytheWise



Series: 2018 Kinktober [11]
Category: Supernatural
Genre: Alpha Benny Lafitte, Alpha Dean, Castiel in Panties, Crossdressing, Getting Back Together, Multi, Omega Castiel, Oral Sex, Sex in the Impala
Language: English
Status: Completed
Published: 2018-10-11
Updated: 2018-10-11
Packaged: 2019-07-29 08:44:42
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,547
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16260707
Author URL: https://archiveofourown.org/users/TobytheWise/pseuds/TobytheWise
Summary: Dean gingerly lets go of Cas and rubs the back of his neck. Before either alphas have time to worry Castiel speaks up. “I shouldn’t have left the way I did.” He kicks at the dirt, staring down at his sparkly chucks. “I got scared. You both were ready to mate me without knowing me. This pull we all feel for each other is just so fucking intense and it freaked me out.” Cas shakes his head, finally looking up at the alphas. “But that didn’t mean it was okay that I bolted without talking to you about it. I’m sorry.”Benny moves forward and touches Castiel’s shoulder. “It’s alright, Cas. We both get it. This isn’t what any of us expected when we decided to take you home that night.” Then he shrugs. “But I’m not sorry that it happened.”Dean cuts in, “and we’d like the chance to actually get to know you. If that’s something you’d like?”





	Day Eleven: Crossdressing

**Author's Note:**

> This story is a continuation from Day Four. If you haven't read day four first I would recommend it :)

Castiel walks towards the coffee shop, needing his pumpkin spiced latte if he’s planning on getting through the day. He’s dressed himself up today hoping it would help get him out of his funk but nothing seems to be working. 

It’s been three weeks since he met and slept with Dean and Benny. He walked out that night thinking he’d never look back. They had both been so tempting, so beautiful, so kind; but things moved so fucking fast it scared Castiel. Their eyes had flashed red and their teeth had elongated like they were going to mate him after knowing each other for a few hours. It was too much so Cas ran. And he regrets not staying and at least talking to them in the morning. His heart is so fucking heavy now. He misses his alphas because yes, they are his alphas. Castiel no longer doubts the instant pull, the impossible lust, the way they had felt so perfect like Cas was clicking into their relationship without a hitch. 

Cas runs his fingers through his hair as he steps up to the door of the coffee shop only to run head first into a muscular chest. Suddenly, Castiel feels like he’s underwater because it’s THAT scent again. Warm apple pie. Fuck.

“Cas?” Dean’s voice asks as his big warms catch Cas. 

Cas looks up into those green eyes and his knees go weak in relief. He’s been trying to think of a way to go back to their apartment and talk things out but he’d been too scared. Now he has his chance thrusts into his lap. 

“Dean,” Cas breathes, a smile slowly forming on his lips. “I’m so glad I ran into you. Is Benny here, too?”

From behind Dean, Benny steps out into Cas’ line of vision. He gives Cas a warm smile that makes his belly fill with butterflies and his smile grow impossibly bigger. 

Dean gingerly lets go of Cas and rubs the back of his neck. Before either alphas have time to worry Castiel speaks up. “I shouldn’t have left the way I did.” He kicks at the dirt, staring down at his sparkly chucks. “I got scared. You both were ready to mate me without knowing me. This pull we all feel for each other is just so fucking intense and it freaked me out.” Cas shakes his head, finally looking up at the alphas. “But that didn’t mean it was okay that I bolted without talking to you about it. I’m sorry.”

Benny moves forward and touches Castiel’s shoulder. “It’s alright, Cas. We both get it. This isn’t what any of us expected when we decided to take you home that night.” Then he shrugs. “But I’m not sorry that it happened.”

Dean cuts in, “and we’d like the chance to actually get to know you. If that’s something you’d like?”

Cas smiles. “Yes.” Then his smiles turns feral. “And I’d also like a repeat of that night. If you’re both up for it.”

Dean pulls his keys out of his pocket, jingling them. “Then come on, omega. We can talk over dinner and see where the night takes us.”

Cas threads his fingers through Benny’s and follows Dean to his car. The weight of Benny’s hand in his feels so fucking right it makes Cas’ chest ache with the thought of all those weeks they lost while he was acting so stubborn and scared. Well, he’s changing that right now. 

“You want the front, Darlin’?” Benny asks. 

Castiel gives him a grin before shaking his head and pulling the alpha into the backseat with him. When Cas looks up, his eyes meet Dean’s through the rearview mirror. Dean smiles and says, “you look really pretty today, Cas.”

Cas feels his face flush. He wasn’t sure what the alphas would think of his outfit; a blue button up blouse, a short jean skirt, and his sparkly chucks. He’d shaved himself bare too along with doing some eyeliner and mascara before leaving the house. Castiel’s insides turn to goo as both alphas share how pretty and beautiful he looks like this. Fuck, they really are perfect.

“Thank you,” he shyly whispers. 

Benny places his finger under Cas’ chin so he’s forced to look into those crystal blue eyes. “You look so beautiful, Cher. You have no idea how much I want you right now.” Benny punctuates his statement with a kiss to Cas’ lips. 

“Then have me,” Cas whispers against his lips, feeling bold surrounded by their scents again after being away for so long. 

Benny wastes no time pulling Castiel into a searing kiss. Cas opens his lips immediately, allowing Benny access to the inside of his mouth. Their tongues meet and Castiel finally gets a taste of his alpha that he’s been craving for weeks. He moans into the kiss, wanting so much more. 

“Fuck,” Dean gasps from the front seat. Cas pulls away and looks up at him, seeing Dean’s face flushed with arousal. “Keep going, baby. Remind our omega of what he’s been missing.”

Cas groans as Benny’s big hands caress his hairless legs. The sensation causes lust to pool in Cas’ belly and his ass already is beginning to slick. Cas leans over and buries his face in Benny’s neck, inhaling his spicy chocolate scent. 

“Benny,” Cas gasps out as the alpha’s hand begins to reach up Cas’ skirt. 

Cas pulls back so he can kiss the alpha, all passion and lust. The smell of their arousal and want filling the car. 

“Can I suck you off, Cas?” Benny asks causing Dean to groan in the front seat. Castiel vigorously nods, pulling his skirt up around his waist. Benny gasps as he takes in Cas’ lacy black panties. “Fuck, Cher, these are mighty pretty.”

“What’s that?” Dean asks.

“Cas is wearing sexy panties for us.” 

“You planning on doing something other than look, Alpha?” Cas taunts, hoping to provoke Benny into touching him. It works because Benny strokes his hard cock through the lace. “Fuck! Please Alpha. Please suck me.”

“Come on, Benny,” Dean murmurs from the front, eyes meeting Cas’ through the rear view mirror. “I think he’s waited long enough.”

Benny tugs Cas’ panties down his legs until they’re completely off. Then he tosses them into Dean’s lap where the alpha picks them up and sniffs them.

“Shit,” Cas breathes, his cock twitching at the display. He keeps one foot down in the well of the backseat and the other he lifts and leans against the back of the seat, exposing himself fully to Benny. 

“Mmm,” Benny hums before leaning down and licking the crown of Castiel’s cock, lapping up the precome that’s been oozing out. “You taste divine.”

“Please,” Cas moans out, his whole body tense with anticipation. Thankfully, Benny doesn’t make him wait long. He takes Cas’ entire cock into his mouth. “Oh fuck,” he grits out through clenched teeth as Benny swallows around the head.

Cas takes Benny’s hat off so he can run his fingers through his hair. Benny’s warm, wet mouth feels so fucking good. Cas tips his head back and lets out another moan. He thrusts his hips up, trying to bury his cock even further but one of Benny’s big hands holds down his hip. 

“Please, want your fingers inside me, Benny.”

Dean groans, hungry eyes darting back every once in awhile to watch them together.

Benny’s finger comes down and touches Cas’ wet hole. He swirls it around Cas’ slick, rubbing against his entrance without ever sliding in. It’s maddening. “No teasing, Alpha. Need it!” Cas cries, head tilted towards the ceiling. 

Benny gives a dark chuckles before sliding his finger all the way in while also swallowing down his cock at the same time. He’s already so fucking close. Benny pulls back before thrusting two fingers in. His fingers are so much bigger than Cas’, stretching him and touching his prostate in the most perfect way. 

“Fuck. So close, Benny. Gonna come down your throat.”

“Yes. Come in my mouth, omega. Let me taste you,” Benny demands before going back to sucking Cas off. 

“Come, Cas,” Dean says from the front seat and Castiel can’t hold out any longer. He curls his fingers tightly into Benny’s hair, letting out a cry of pleasure as he empties his load into Benny’s mouth. His knees clamp shut tight around Benny’s head as the pleasure overwhelms him.

As Cas slumps back into the seat, Benny sits up with a giant grin on his face. They’re at a red light so Benny pulls Dean head around, bringing his glistening fingers to Dean’s mouth. The alpha sucks on them greedily, taking all of Cas’ slick that he can. 

“Fuck,” Cas whispers as he watches. These two are exactly what Cas has always hoped for when he’s thought about his future mate. 

A horn from behind them gets them focused on making it to their house. Once Cas has fixed his skirt back into place he scoots over by Benny, curling up at his side. Benny wraps an arm around Cas, soothingly rubbing his back and arm. The smell of content omega beginning to permeate the air inside the car. 

Cas thinks he could get used to this.

**Author's Note:**

> These three will have at least one more day together coming up :)


End file.
